Nyuzenamide C, an Antiangiogenic Epoxy Cinnamic Acid-Containing Bicyclic Peptide from a Riverine Streptomyces sp.

Joon Soo An; Myoun Su Kim; Jaeho Han; Sung Chul Jang; Ji Hyeon Im; Jinsheng Cui; Yeonjin Lee; Sang Jip Nam; Jongheon Shin; Sang Kook Lee; Yeo Joon Yoon; Dong Chan Oh

doi:10.1021/acs.jnatprod.1c00837

Nyuzenamide C, an Antiangiogenic Epoxy Cinnamic Acid-Containing Bicyclic Peptide from a Riverine Streptomyces sp.

Joon Soo An
, Myoun Su Kim
, Jaeho Han
, Sung Chul Jang
, Ji Hyeon Im
, Jinsheng Cui
, Yeonjin Lee
, Sang Jip Nam
, Jongheon Shin
, Sang Kook Lee
, Yeo Joon Yoon
, Dong Chan Oh

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Review article › peer-review

21 Scopus citations

Abstract

A new nonribosomal peptide, nyuzenamide C (1), was discovered from riverine sediment-derived Streptomyces sp. DM14. Comprehensive analysis of the spectroscopic data of nyuzenamide C (1) revealed that 1 has a bicyclic backbone composed of six common amino acid residues (Asn, Leu, Pro, Gly, Val, and Thr) and four nonproteinogenic amino acid units, including hydroxyglycine, β-hydroxyphenylalanine, p-hydroxyphenylglycine, and 3,β-dihydroxytyrosine, along with 1,2-epoxypropyl cinnamic acid. The absolute configuration of 1 was proposed by J-based configuration analysis, the advanced Marfey's method, quantum mechanics-based DP4 calculations, and bioinformatic analysis of its nonribosomal peptide synthetase biosynthetic gene cluster. Nyuzenamide C (1) displayed antiangiogenic activity in human umbilical vein endothelial cells and induced quinone reductase in murine Hepa-1c1c7 cells.

Original language	English
Pages (from-to)	804-814
Number of pages	11
Journal	Journal of Natural Products
Volume	85
Issue number	4
DOIs	https://doi.org/10.1021/acs.jnatprod.1c00837
State	Published - 22 Apr 2022

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@article{b550b07b43264cc29e8723ad5e0753a1,

title = "Nyuzenamide C, an Antiangiogenic Epoxy Cinnamic Acid-Containing Bicyclic Peptide from a Riverine Streptomyces sp.",

abstract = "A new nonribosomal peptide, nyuzenamide C (1), was discovered from riverine sediment-derived Streptomyces sp. DM14. Comprehensive analysis of the spectroscopic data of nyuzenamide C (1) revealed that 1 has a bicyclic backbone composed of six common amino acid residues (Asn, Leu, Pro, Gly, Val, and Thr) and four nonproteinogenic amino acid units, including hydroxyglycine, β-hydroxyphenylalanine, p-hydroxyphenylglycine, and 3,β-dihydroxytyrosine, along with 1,2-epoxypropyl cinnamic acid. The absolute configuration of 1 was proposed by J-based configuration analysis, the advanced Marfey's method, quantum mechanics-based DP4 calculations, and bioinformatic analysis of its nonribosomal peptide synthetase biosynthetic gene cluster. Nyuzenamide C (1) displayed antiangiogenic activity in human umbilical vein endothelial cells and induced quinone reductase in murine Hepa-1c1c7 cells.",

author = "An, \{Joon Soo\} and Kim, \{Myoun Su\} and Jaeho Han and Jang, \{Sung Chul\} and Im, \{Ji Hyeon\} and Jinsheng Cui and Yeonjin Lee and Nam, \{Sang Jip\} and Jongheon Shin and Lee, \{Sang Kook\} and Yoon, \{Yeo Joon\} and Oh, \{Dong Chan\}",

year = "2022",

month = apr,

day = "22",

doi = "10.1021/acs.jnatprod.1c00837",

language = "English",

volume = "85",

pages = "804--814",

journal = "Journal of Natural Products",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Nyuzenamide C, an Antiangiogenic Epoxy Cinnamic Acid-Containing Bicyclic Peptide from a Riverine Streptomyces sp.

AU - An, Joon Soo

AU - Kim, Myoun Su

AU - Han, Jaeho

AU - Jang, Sung Chul

AU - Im, Ji Hyeon

AU - Cui, Jinsheng

AU - Lee, Yeonjin

AU - Nam, Sang Jip

AU - Shin, Jongheon

AU - Lee, Sang Kook

AU - Yoon, Yeo Joon

AU - Oh, Dong Chan

PY - 2022/4/22

Y1 - 2022/4/22

N2 - A new nonribosomal peptide, nyuzenamide C (1), was discovered from riverine sediment-derived Streptomyces sp. DM14. Comprehensive analysis of the spectroscopic data of nyuzenamide C (1) revealed that 1 has a bicyclic backbone composed of six common amino acid residues (Asn, Leu, Pro, Gly, Val, and Thr) and four nonproteinogenic amino acid units, including hydroxyglycine, β-hydroxyphenylalanine, p-hydroxyphenylglycine, and 3,β-dihydroxytyrosine, along with 1,2-epoxypropyl cinnamic acid. The absolute configuration of 1 was proposed by J-based configuration analysis, the advanced Marfey's method, quantum mechanics-based DP4 calculations, and bioinformatic analysis of its nonribosomal peptide synthetase biosynthetic gene cluster. Nyuzenamide C (1) displayed antiangiogenic activity in human umbilical vein endothelial cells and induced quinone reductase in murine Hepa-1c1c7 cells.

AB - A new nonribosomal peptide, nyuzenamide C (1), was discovered from riverine sediment-derived Streptomyces sp. DM14. Comprehensive analysis of the spectroscopic data of nyuzenamide C (1) revealed that 1 has a bicyclic backbone composed of six common amino acid residues (Asn, Leu, Pro, Gly, Val, and Thr) and four nonproteinogenic amino acid units, including hydroxyglycine, β-hydroxyphenylalanine, p-hydroxyphenylglycine, and 3,β-dihydroxytyrosine, along with 1,2-epoxypropyl cinnamic acid. The absolute configuration of 1 was proposed by J-based configuration analysis, the advanced Marfey's method, quantum mechanics-based DP4 calculations, and bioinformatic analysis of its nonribosomal peptide synthetase biosynthetic gene cluster. Nyuzenamide C (1) displayed antiangiogenic activity in human umbilical vein endothelial cells and induced quinone reductase in murine Hepa-1c1c7 cells.

UR - https://www.scopus.com/pages/publications/85127267245

U2 - 10.1021/acs.jnatprod.1c00837

DO - 10.1021/acs.jnatprod.1c00837

M3 - Review article

C2 - 35294831

AN - SCOPUS:85127267245

SN - 0163-3864

VL - 85

SP - 804

EP - 814

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 4

ER -

Nyuzenamide C, an Antiangiogenic Epoxy Cinnamic Acid-Containing Bicyclic Peptide from a Riverine Streptomyces sp.

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